US4464276A - Polyoxyalkylene polyamine triazole complexes - Google Patents
Polyoxyalkylene polyamine triazole complexes Download PDFInfo
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- US4464276A US4464276A US06/492,313 US49231383A US4464276A US 4464276 A US4464276 A US 4464276A US 49231383 A US49231383 A US 49231383A US 4464276 A US4464276 A US 4464276A
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- calcium
- complex
- benzotriazole
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- 229920000768 polyamine Polymers 0.000 title claims abstract description 7
- 150000003852 triazoles Chemical class 0.000 title abstract description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 25
- 239000011575 calcium Substances 0.000 claims description 25
- 229910052791 calcium Inorganic materials 0.000 claims description 25
- -1 hydrocarbon radical Chemical class 0.000 claims description 11
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 10
- 239000012964 benzotriazole Substances 0.000 claims description 10
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 9
- JSIAIROWMJGMQZ-UHFFFAOYSA-N 2h-triazol-4-amine Chemical compound NC1=CNN=N1 JSIAIROWMJGMQZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 6
- 239000000314 lubricant Substances 0.000 claims description 6
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000003921 oil Substances 0.000 abstract description 17
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 23
- 239000000654 additive Substances 0.000 description 12
- 230000007797 corrosion Effects 0.000 description 12
- 238000005260 corrosion Methods 0.000 description 12
- 238000009472 formulation Methods 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 230000001590 oxidative effect Effects 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 150000004707 phenolate Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000004580 weight loss Effects 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000008186 active pharmaceutical agent Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 230000005484 gravity Effects 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000010687 lubricating oil Substances 0.000 description 3
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- NBXLZXKFNRWJSI-UHFFFAOYSA-N 1-(2h-triazol-4-yl)propan-2-amine Chemical compound CC(N)CC=1C=NNN=1 NBXLZXKFNRWJSI-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- ZIFJZWXEACSTMH-UHFFFAOYSA-N 2h-benzotriazol-4-ylmethanamine Chemical compound NCC1=CC=CC2=C1N=NN2 ZIFJZWXEACSTMH-UHFFFAOYSA-N 0.000 description 1
- CUQWNLQYKNITFP-UHFFFAOYSA-N C=C.C=C.C=C.C1(CCC(N1)=O)=O Chemical group C=C.C=C.C=C.C1(CCC(N1)=O)=O CUQWNLQYKNITFP-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 101150108015 STR6 gene Proteins 0.000 description 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- WIKSRXFQIZQFEH-UHFFFAOYSA-N [Cu].[Pb] Chemical compound [Cu].[Pb] WIKSRXFQIZQFEH-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 239000010710 diesel engine oil Substances 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- NHWGPUVJQFTOQX-UHFFFAOYSA-N ethyl-[2-[2-[ethyl(dimethyl)azaniumyl]ethyl-methylamino]ethyl]-dimethylazanium Chemical compound CC[N+](C)(C)CCN(C)CC[N+](C)(C)CC NHWGPUVJQFTOQX-UHFFFAOYSA-N 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000011133 lead Chemical group 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical group NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 125000004385 trihaloalkyl group Chemical group 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 239000010913 used oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/223—Five-membered rings containing nitrogen and carbon only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
- C10M2215/226—Morpholines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
- C10M2215/30—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/252—Diesel engines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/252—Diesel engines
- C10N2040/253—Small diesel engines
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
- F02B3/00—Engines characterised by air compression and subsequent fuel addition
- F02B3/06—Engines characterised by air compression and subsequent fuel addition with compression ignition
Definitions
- This invention relates to triazole derivatives and to fluid compositions containing same which are specially designed for use between two relatively moving surfaces for reducing friction therebetween and preserving the surfaces. More specifically, the invention discloses improved diesel lubricant compositions which impart superior oxidative stability and corrosion control to a medium speed, diesel engine oil containing a calcium carbonate overbased sulfurized calcium alkylphenolate.
- these detergents were replaced by calcium sulfurized phenolates made by a process utilizing lime as the source of calcium whereby the solvents system is eliminated and the disposed residue meets EPA regulations.
- These phenolates can be denominated 1/1 calcium carbonate overbased sulfurized calcium alkylphenolates and 2/1 overbased sulfurized calcium alkylphenolates containing calcium sulfonate.
- These detergents-dispersants do not however, provide the corrosion protection or oxidative stability medium speed diesel engine formulations that the calcium reagent produced phenolates provided. In order to attain the original performance with the lime prepared phenolates, it is necessary now to supplement the formulation with a corrosion and/or oxidation inhibitor.
- U.S. Pat. No. 4,278,553 shows a corrosion inhibitor consisting of a benzotriazole, N-alkyl-1,3-propane diamine-formaldehyde condensation product.
- U.S. Pat. No. 4,285,823 shows a diesel lubricant composition comprising an oil corrosion inhibited by the incorporation of an N-substituted-5-amino-1H-tetrazole. While the above may be considered the most relevant prior art, there is no suggestion therein of the additives of this invention.
- the invention provides novel polyoxyalkylene polyamine-triazole complexes having utility as diesel oil additives and which are represented generically by the following formula: ##STR1## wherein Y is hydrogen or a (lower) alkyl radical having 1 to 5 carbon atoms; Z is a hydrocarbon radical having 2 to 10, and, preferably 4 carbon atoms, forming from 1 to 4 external ether linkages including lower alkyl, amino (lower) alkyl and ureido (lower) alkyl; n is a number from about 1 to about 15 and r is a number from 1 to 4; A is 5-aminotriazole or benzotriazole; B is NH 2 or ureido (--NHCONH 2 ) except that when Z is ureido (lower) alkyl and B is ureido, r can only be 1.
- the invention also provides diesel lubricating oils containing at least one of the above additives together with an effective amount of a 1/1 calcium carbonate overbased sulfurized calcium alkylphenolate or of a 2/1 overbased sulfurized calcium alkylphenolate containing calcium sulfonate serving as a detergent inhibitor.
- the lubricant compositions of the invention have a TBN or total base number defined as the quantity of acid expressed in terms of the equivalent number of milligrams of potassium hydroxide that is required to neutralize oil basic constituence present in one gram of a given sample as evaluated by ASTM method D664 of at least 5 owing to the presence therein of conventional additives and are thus capable of preventing corrosion by sludge formed by oxidative deterioration of oil at the high temperatures existing under normal conditions of engine use in proximity to the combustion chamber.
- TBN or total base number defined as the quantity of acid expressed in terms of the equivalent number of milligrams of potassium hydroxide that is required to neutralize oil basic constituence present in one gram of a given sample as evaluated by ASTM method D664 of at least 5 owing to the presence therein of conventional additives and are thus capable of preventing corrosion by sludge formed by oxidative deterioration of oil at the high temperatures existing under normal conditions of engine use in proximity to the combustion chamber.
- Preparation of the complexes used in a diesel lubricating composition according to this invention is relatively uncomplicated and can be economically conducted.
- the preparation entails mixing at room temperature with thorough agitation one part by weight of a triazole with from 40 to 160 parts by weight at least one polyoxyalkylene polyamine depicted by the formula: ##STR2## wherein Y, Z, n and r are as above.
- the most preferred polyoxyalkylene polyamines are the polyoxypropylenediamines wherein Y is a methyl radical, n is a number from 1 to 3, Z is a 2-amino propylene radical and r is 1.
- These polyoxyalkylene polyamines can be prepared by known methods as disclosed in U.S. Pat. Nos. 3,236,895 and 3,654,370 and are sold under the trademark name of "Jeffamines" by Jefferson Chemical Co., Austin, Tex. Some of these are sold as mixtures of amines.
- the triazole reactant can be 5-aminotriazole or benzotriazole or derivatives thereof bearing noninterfering, inert substituents such as alkyl, nitro, cyano, trihaloalkyl and the like.
- the effectiveness of the additives of the invention was tested by the Union Pacific Oxidation Test (UPOT). This test is used by railroads to judge the acceptability of an oil for use in their equipment. The test measures corrosion (50 mg. max. limit) and oxidative stability (20% max. viscosity increase at 100° F.) as well as other used oil parameters (pH-which is used by some railroads to judge the oil drain interval-below 5, drain; above 5, satisfactory; TBN can be used as a measure of alkaline retention). The test method involves bubbling 5 liters of oxygen per hour through 300 mls. of test oil composition at 285° F. in which there is immersed a 1 ⁇ 3 ⁇ 0.06 inch steel backed copper-lead test specimen cut from bearing stock.
- UPOT Union Pacific Oxidation Test
- the viscosity of the test oil is measured before and after the 144 hour test period and the greater the difference in viscosity the greater the oxidative deterioration of the sulfurized calcium alkylphenolate composition.
- the test specimen is weighed before and after the test period and the greater the weight loss of test specimen the greater the corrosive deterioration of the test formulation. The larger the amount of copper, iron and lead moieties found in the oil after test, the greater the corrosive deterioration thereof.
- the complexes of this invention are used in an amount ranging from 0.5 to 3 weight percent of the oil and the sulfurized calcium alkylphenolate ingredient in finished (dilute) lubricating oil compositions employed for engine use in desirably between about 0.1 and 7.5 weight percent with a calcium concentration of between about 0.06 and 0.5 weight percent, preferably about 0.1 and 0.4 weight percent.
- the concentrates can be formed for storage and transport and are subsequently blended to finished oil composition for engine use having a sulfurized calcium alkylphenolate of between about 0.1 and 10 weight percent.
- additives may be included such as supplementary dispersants, pour depressors, antioxidants, viscosity index improvers, oleagenous agents and antifoamant mixtures thereof.
- supplementary dispersants such as phenol, phenol, phenol, phenol, phenol, phenol, phenol, phenol, phenol, phenol, phenol, phenol, phenol, phenol, phenol, phenol, phenol, phenol, phenolate, oleagenous agents and antifoamant mixtures thereof.
- lubricants for railway diesel engines are lubricants for railway diesel engines.
- a preferred class of dispersant additives is derivative of alkylene succinimide polyamides characterized by the formula: ##STR3## where R 2 is alkenyl of from 50 to 200 carbons, x is an integer of from 0 to 10.
- R 2 is alkenyl of from 50 to 200 carbons
- x is an integer of from 0 to 10.
- the alkylene group is polybutene having a molecular weight of about 1200 and the polyamine is tetraethylene pentamine.
- a preferred antifoamant is a methyl silicone polymer (12500 cs at 770° F.) in kerosene.
- a preferred pour depressant is a polymethacrylate.
- A is a solvent neutral oil having an API gravity about 31
- B is a solvent neutral oil having an API gravity of 26.5-29.0
- C is a pale oil having an API gravity of 19 to 22
- D is a 1 to 1 calcium carbonate overbased sulfurized calcium alkylphenolate
- E is an alkenyl succinimide triethylene pentamine
- F is a chlorinated n-paraffin containing 60% of chlorine
- G is a methacrylate polymer
- H is a blend of silicone and crystallite.
- a typical 10 TBN medium speed diesel lubricant (A) gave a corrosion value of 280 mg in the UPOT test which was reduced in (B) by the addition of 2% of the additive.
- the product can be generally represented as the following: ##STR5##
- the product was characterized by ultraviolet spectra as follows:
- the Jeffamine BUD 2000 had a max. abs. of 2.15 at 210 nm (MCOH)
- Benzotriazole showed: max. abs. 2.39 at 203 nm, 1.68 at 253 nm, 1.35 at 275 nm.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
Abstract
Novel polyoxyalkylene polyamine triazole or benzotriazole complexes for diesel oils used in medium speed diesel engines.
Description
This invention relates to triazole derivatives and to fluid compositions containing same which are specially designed for use between two relatively moving surfaces for reducing friction therebetween and preserving the surfaces. More specifically, the invention discloses improved diesel lubricant compositions which impart superior oxidative stability and corrosion control to a medium speed, diesel engine oil containing a calcium carbonate overbased sulfurized calcium alkylphenolate.
Earlier formulations of this type contained various calcium sulfurized alkylphenolates which were designed to provide the finished oil with improved corrosion protection and/or oxidative stability. These phenolates included sulfurized CO2 -blown, double neutralized, normal calcium alkylphenolate, 2/1 overbased Ca(OH)2 sulfurized calcium alkylphenolate and calcium reagent neutralized, sulfurized calcium alkylphenolate overbased by the hydrolysis of calcium reagent and blown with CO2 for complete carbonation. These all were made by a process which employed a solvent recovery procedure which was expensive and wherein some of the byproducts that were trapped in the filter cake were hazardous to the environment upon disposal and did not meet EPA requirements. Accordingly, these detergents were replaced by calcium sulfurized phenolates made by a process utilizing lime as the source of calcium whereby the solvents system is eliminated and the disposed residue meets EPA regulations. These phenolates can be denominated 1/1 calcium carbonate overbased sulfurized calcium alkylphenolates and 2/1 overbased sulfurized calcium alkylphenolates containing calcium sulfonate. These detergents-dispersants do not however, provide the corrosion protection or oxidative stability medium speed diesel engine formulations that the calcium reagent produced phenolates provided. In order to attain the original performance with the lime prepared phenolates, it is necessary now to supplement the formulation with a corrosion and/or oxidation inhibitor.
The prior art to which this invention relates evidences activity and includes coassigned U.S. Pat. Nos. 4,285,823, 4,320,016, 4,285,823, 4,169,799 and 4,172,269, the disclosures of which are incorporated herein by reference for their showing of diesel engine lubricant constituents.
Of these, U.S. Pat. No. 4,278,553 shows a corrosion inhibitor consisting of a benzotriazole, N-alkyl-1,3-propane diamine-formaldehyde condensation product. U.S. Pat. No. 4,285,823 shows a diesel lubricant composition comprising an oil corrosion inhibited by the incorporation of an N-substituted-5-amino-1H-tetrazole. While the above may be considered the most relevant prior art, there is no suggestion therein of the additives of this invention.
The invention provides novel polyoxyalkylene polyamine-triazole complexes having utility as diesel oil additives and which are represented generically by the following formula: ##STR1## wherein Y is hydrogen or a (lower) alkyl radical having 1 to 5 carbon atoms; Z is a hydrocarbon radical having 2 to 10, and, preferably 4 carbon atoms, forming from 1 to 4 external ether linkages including lower alkyl, amino (lower) alkyl and ureido (lower) alkyl; n is a number from about 1 to about 15 and r is a number from 1 to 4; A is 5-aminotriazole or benzotriazole; B is NH2 or ureido (--NHCONH2) except that when Z is ureido (lower) alkyl and B is ureido, r can only be 1.
The invention also provides diesel lubricating oils containing at least one of the above additives together with an effective amount of a 1/1 calcium carbonate overbased sulfurized calcium alkylphenolate or of a 2/1 overbased sulfurized calcium alkylphenolate containing calcium sulfonate serving as a detergent inhibitor.
The lubricant compositions of the invention have a TBN or total base number defined as the quantity of acid expressed in terms of the equivalent number of milligrams of potassium hydroxide that is required to neutralize oil basic constituence present in one gram of a given sample as evaluated by ASTM method D664 of at least 5 owing to the presence therein of conventional additives and are thus capable of preventing corrosion by sludge formed by oxidative deterioration of oil at the high temperatures existing under normal conditions of engine use in proximity to the combustion chamber.
Preparation of the complexes used in a diesel lubricating composition according to this invention is relatively uncomplicated and can be economically conducted. The preparation entails mixing at room temperature with thorough agitation one part by weight of a triazole with from 40 to 160 parts by weight at least one polyoxyalkylene polyamine depicted by the formula: ##STR2## wherein Y, Z, n and r are as above. The most preferred polyoxyalkylene polyamines are the polyoxypropylenediamines wherein Y is a methyl radical, n is a number from 1 to 3, Z is a 2-amino propylene radical and r is 1. These polyoxyalkylene polyamines can be prepared by known methods as disclosed in U.S. Pat. Nos. 3,236,895 and 3,654,370 and are sold under the trademark name of "Jeffamines" by Jefferson Chemical Co., Austin, Tex. Some of these are sold as mixtures of amines.
The triazole reactant can be 5-aminotriazole or benzotriazole or derivatives thereof bearing noninterfering, inert substituents such as alkyl, nitro, cyano, trihaloalkyl and the like.
The effectiveness of the additives of the invention was tested by the Union Pacific Oxidation Test (UPOT). This test is used by railroads to judge the acceptability of an oil for use in their equipment. The test measures corrosion (50 mg. max. limit) and oxidative stability (20% max. viscosity increase at 100° F.) as well as other used oil parameters (pH-which is used by some railroads to judge the oil drain interval-below 5, drain; above 5, satisfactory; TBN can be used as a measure of alkaline retention). The test method involves bubbling 5 liters of oxygen per hour through 300 mls. of test oil composition at 285° F. in which there is immersed a 1×3×0.06 inch steel backed copper-lead test specimen cut from bearing stock. The viscosity of the test oil is measured before and after the 144 hour test period and the greater the difference in viscosity the greater the oxidative deterioration of the sulfurized calcium alkylphenolate composition. In addition, the test specimen is weighed before and after the test period and the greater the weight loss of test specimen the greater the corrosive deterioration of the test formulation. The larger the amount of copper, iron and lead moieties found in the oil after test, the greater the corrosive deterioration thereof.
The complexes of this invention are used in an amount ranging from 0.5 to 3 weight percent of the oil and the sulfurized calcium alkylphenolate ingredient in finished (dilute) lubricating oil compositions employed for engine use in desirably between about 0.1 and 7.5 weight percent with a calcium concentration of between about 0.06 and 0.5 weight percent, preferably about 0.1 and 0.4 weight percent. The concentrates can be formed for storage and transport and are subsequently blended to finished oil composition for engine use having a sulfurized calcium alkylphenolate of between about 0.1 and 10 weight percent.
In the finished lubricating oil compositions, other additives may be included such as supplementary dispersants, pour depressors, antioxidants, viscosity index improvers, oleagenous agents and antifoamant mixtures thereof. Exactly what other additives are included in the finished oil and the particular amounts therein will, of course, depend on the particular use the finished product is to be put to. One of the most suitable uses found for the overbased calcium alkylphenolate produced herein are lubricants for railway diesel engines.
A preferred class of dispersant additives is derivative of alkylene succinimide polyamides characterized by the formula: ##STR3## where R2 is alkenyl of from 50 to 200 carbons, x is an integer of from 0 to 10. Preferably, the alkylene group is polybutene having a molecular weight of about 1200 and the polyamine is tetraethylene pentamine.
A preferred antifoamant is a methyl silicone polymer (12500 cs at 770° F.) in kerosene.
A preferred pour depressant is a polymethacrylate.
The following examples further illustrate the invention but are not to be construed as limitations thereof.
Preparation of polyoxypropylenediamine (molecular weight 360)-5-aminotriazole complex.
49.5 parts of the above amine (Jeffamine M-360) and 0.5 parts of 5-aminotriazole were mixed throughly for half hour at room temperature and the complex was isolated.
The complex above prepared can be generally represented as the following: ##STR4## U.V. spectra confirmed the above structure as follows:
UV Analysis of Aminotriazole-Jeffamine M-360 Complex:
Complex: Max. abs. 2.67 at 194 nm
ATZ: Max. abs. 2.82 at 210 nm
Jeffamine M-360: Max. abs. 2.61 at 210 nm
In the table below and in the tables following the other examples showing the medium speed diesel engine performance of formulations with and without the present additive, the constituents are identified by the following letters: A is a solvent neutral oil having an API gravity about 31, B is a solvent neutral oil having an API gravity of 26.5-29.0, C is a pale oil having an API gravity of 19 to 22, D is a 1 to 1 calcium carbonate overbased sulfurized calcium alkylphenolate, E is an alkenyl succinimide triethylene pentamine, F is a chlorinated n-paraffin containing 60% of chlorine, G is a methacrylate polymer, H is a blend of silicone and crystallite.
The above complex was tested in the UPOT test in formulation B below and reduced the corrosion value of a 10 TBN oil from 280 to 38 mg.
______________________________________
(A) (B)
______________________________________
Composition, Wt. %
A 5.00 5.00
B 48.30 46.30
C 37.00 37.00
D 5.55 5.55
E 4.05 4.05
F 0.05 0.05
G 0.05 0.05
H 150 150
Experimental Additive of Ex. 1
-- 2.00
Union Pacific Oxidation
Test
Weight Loss, mg. 280 38
Viscosity Increase, %
160 51
______________________________________
Preparation of "Jeffamine D230"-5-aminotriazole complex.
49.5 parts of the above amine which has a molecular weight of 230 and 0.5 parts of 5-aminotriazole were stirred thoroughly for 1/2 hr. at room temperature and product was isolated.
A typical 10 TBN medium speed diesel lubricant (A) gave a corrosion value of 280 mg in the UPOT test which was reduced in (B) by the addition of 2% of the additive.
______________________________________
(A) (B)
8847.00
8848.20
______________________________________
Composition, Wt. %
A 5.00 5.00
B 48.30 46.30
C 37.00 37.00
D 5.55 5.55
E 4.05 4.05
F 0.05 0.05
G 0.05 0.05
H 150 150
Additive of Ex. 2 -- 2.00
Union Pacific Oxidation
Test
Weight Loss, mg. 280 81
______________________________________
The product can be generally represented as the following: ##STR5## The product was characterized by ultraviolet spectra as follows:
U.V. Analysis of Jeffamine D-230-Aminotriazole+Max. abs. 2.63 at 199 nm
Jeffamine D-230: Max. abs. 2.85 at 213 nm Max. abs. 2.82 at 210 nm for 5-aminotriazole
The existance of the complex is proved by the shift in the U.V. spectra.
Preparation of "Jeffamine D230" benzotriazole complex.
49.5 parts of "Jeffamine D230" having a molecular of 230 was mixed with thorough stirring with 0.5 parts of benzotriazole at room temperature for 1/2 hr. The complex was isolated and tested as shown below. It reduced the corrosion value from 280 to 152.
______________________________________
(A) (B)
______________________________________
Composition, Wt. %
A 5.00 5.00
B 48.30 46.30
C 37.00 37.00
D 5.55 5.55
E 4.05 4.05
F 0.05 0.05
G 0.05 0.05
H 150 150
Ex. 3 -- 2.00
Complex
Union Pacific Oxidation
Test
Weight Loss, mg. 280 152
______________________________________
The complex was verified by U.V. It can be generally represented by the following: ##STR6##
U.V. Analysis of Jeffamine D-230-Benzotriole Complex=Max. abs. 2.85 at 206 nm 2nd Max. abs. 0.99 at 273 nm
Benzotriole: Max. abs. 2.38 at 200 nm 2nd Max. abs. 0.80 at 259 nm
Jeffamine D-230: Max. abs. 2.85 at 213 nm
Preparation of "Jeffamine BUD-2000"-benzotriazole complex.
49.5 parts of "Jeffamine BUD-2000" and 0.5 parts of benzotriazole were stirred thoroughly for 1/2 hr. at room temperature and the product was isolated.
As verified by U.V. analysis the complex had the formula: ##STR7##
It showed maximum absorption of 2.73 at 210 nm and a second maximum of 1.25 at 254 nm. The Jeffamine BUD 2000 had a max. abs. of 2.15 at 210 nm (MCOH)
Benzotriazole showed: max. abs. 2.39 at 203 nm, 1.68 at 253 nm, 1.35 at 275 nm.
______________________________________
(A) (B)
______________________________________
Composition, Wt. %
A 5.00 5.00
B 48.30 46.30
C 37.00 37.00
D 5.55 5.55
E 4.05 4.05
F 0.05 0.05
G 0.05 0.05
H 150 150
Jeffamine BUD-2000-
-- 2.00
Benzotriazole complex
Union Pacific Oxidation
Test
Weight Loss, mg. 280 152
Viscosity Increase, %
160 93
______________________________________
As shown in the above table, addition of 2 percent by weight of the complex reduced the corrosion value by 280 mg to 152 mg and reduced the viscosity increase to 93%.
The above and other exemplary complexes according to this invention are depicted in tabular form in Table 1 below reference being had to the generic formula given above:
______________________________________
Example
No. Z A B r n
______________________________________
I 2-aminoethyl
5-amino NH.sub.2
1 2-3
II 2-aminopropyl
triazole NH.sub.2
1 2-3
III 2-aminopropyl
benzotriazole
NH.sub.2
2-3 2-3
IV 2-ureidopropyl
benzotriazole
2-ureido-
1 1
propyl
V aminomethyl benzotriazole
NH.sub.2
1 10
VI 3-aminobutyl
benzotriazole
NH.sub.2
1 12
VII 1-ureidoethyl
benzotriazole
NH.sub.2
1 12
______________________________________
The present invention may be embodied in other specific forms without departing from the spirit or essential attributes thereof and, accordingly, reference should be made to the appended claims rather than to the foregoing specification as indicating the scope of the invention.
Claims (6)
1. Polyoxyalkylene polyamine complexes of the formula: ##STR8## wherein A is 5-aminotriazole or benzotriazole; Y is hydrogen, or a lower alkyl group having 1 to 5 carbon atoms; Z is a hydrocarbon radical having 2-10 carbon atoms forming from 1 to 4 external ether linkages; n is 1 to 15 and r is 1 to 4; B is NH2 or ureido except that when Z is ureidoalkyl and B is ureido, r can only be 1.
2. The complexes of claim 1 having the formula: ##STR9## wherein n is 2 to 3.
3. The complexes of claim 1, having the formula: ##STR10## wherein n is 2 to 3.
4. The complexes of claim 1 having the formula: ##STR11## wherein x is 2 or 3.
5. The complexes of claim 1 having the formula: ##STR12##
6. A fully formulated medium speed diesel lubricant having a TBN of at least 5 and containing from 0.5 to 3 weight percent of a complex of claim 1 and 2% to 10% of a 1/1 calcium carbonate overbased sulfurized calcium alkylphenolate or 2/1 overbased sulfurized calcium alkylphenolate containing calcium sulfonate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/492,313 US4464276A (en) | 1983-05-06 | 1983-05-06 | Polyoxyalkylene polyamine triazole complexes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/492,313 US4464276A (en) | 1983-05-06 | 1983-05-06 | Polyoxyalkylene polyamine triazole complexes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4464276A true US4464276A (en) | 1984-08-07 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/492,313 Expired - Fee Related US4464276A (en) | 1983-05-06 | 1983-05-06 | Polyoxyalkylene polyamine triazole complexes |
Country Status (1)
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Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4501677A (en) * | 1983-11-02 | 1985-02-26 | Exxon Research & Engineering Co. | Heterocyclic nitrogen compounds--organometallic salt complexes as corrosion inhibitors in lubricating oils |
| US4676917A (en) * | 1986-02-27 | 1987-06-30 | Texaco Inc. | Railway diesel crankcase lubricant |
| US4705642A (en) * | 1986-06-09 | 1987-11-10 | Texaco Inc. | Haze, oxidation, and corrosion resistant diesel engine lubricant |
| EP0315293A3 (en) * | 1987-11-02 | 1989-09-06 | Texaco Development Corporation | Oxidation and corrosion resistant diesel engine lubricant |
| US4897086A (en) * | 1988-12-29 | 1990-01-30 | Mobil Oil Corporation | Lubricant and fuel compositions containing reaction products of polyalkenyl succinimides, aldehydes, and triazoles |
| US4938883A (en) * | 1988-08-26 | 1990-07-03 | Amoco Corporation | Overbased alkaline earth alkenyl succinates as a silver-mild source of alkalinity for heavy duty diesel engines |
| US4963278A (en) * | 1988-12-29 | 1990-10-16 | Mobil Oil Corporation | Lubricant and fuel compositions containing reaction products of polyalkenyl succinimides, aldehydes, and triazoles |
| US4994197A (en) * | 1989-12-18 | 1991-02-19 | Mobil Oil Corporation | Triazole compositions as fuel and lube additives |
| US5171462A (en) * | 1991-12-23 | 1992-12-15 | Texaco Inc. | Mixtures of polyoxyalkylene ester and aminopolyazoles as oxidation and corrosion resistant lubricant additives |
| US5308521A (en) * | 1992-07-08 | 1994-05-03 | The Lubrizol Corporation | Lubricant with improved anti-corrosion properties |
| US5397486A (en) * | 1993-07-30 | 1995-03-14 | Chevron Chemical Company | Lubricating oil compositions for railroad diesel engines |
| US5457083A (en) * | 1992-10-15 | 1995-10-10 | Calgon Corporation | Synergistic antimicrobial combination of polyether phosphonates and non-oxidizing biocides |
| EP0812833A1 (en) * | 1996-06-10 | 1997-12-17 | Armstrong World Industries, Inc. | Water soluble triazole derivatives and their use as blowing inhibitor in chemical embossing processes |
| US5853435A (en) * | 1994-12-30 | 1998-12-29 | Mobil Oil Corporation | Polymeric amine-heterocyclic reaction products as fuel and lubricant antiwear, detergency and cleanliness additives |
| US5888255A (en) * | 1997-10-10 | 1999-03-30 | Exxon Research And Engineering Co. | Distillate fuel composition of reduced nickel corrosivity |
| US6248701B1 (en) * | 1994-05-13 | 2001-06-19 | Henkel Corporation | Aqueous metal coating composition and process with reduced staining and corrosion |
| US20110293469A1 (en) * | 2010-05-28 | 2011-12-01 | John Richardson | Additive formulation for industrial cooling systems |
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| US4197210A (en) * | 1977-04-22 | 1980-04-08 | Mobil Oil Corporation | Oil-soluble adducts of benzotriazole and dialkylamines and lubricant compositions containing the same |
| US4278553A (en) * | 1980-01-04 | 1981-07-14 | Texaco Inc. | Diesel lubricant containing benzotriazole derivatives |
| US4283296A (en) * | 1978-08-21 | 1981-08-11 | Texaco Inc. | Amine salt of N-triazolyl-hydrocarbyl succinamic acid and lubricating oil composition containing same |
-
1983
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4197210A (en) * | 1977-04-22 | 1980-04-08 | Mobil Oil Corporation | Oil-soluble adducts of benzotriazole and dialkylamines and lubricant compositions containing the same |
| US4144180A (en) * | 1977-10-03 | 1979-03-13 | Mobil Oil Corporation | Derivatives of triazole as load-carrying additives for gear oils |
| US4283296A (en) * | 1978-08-21 | 1981-08-11 | Texaco Inc. | Amine salt of N-triazolyl-hydrocarbyl succinamic acid and lubricating oil composition containing same |
| US4278553A (en) * | 1980-01-04 | 1981-07-14 | Texaco Inc. | Diesel lubricant containing benzotriazole derivatives |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4501677A (en) * | 1983-11-02 | 1985-02-26 | Exxon Research & Engineering Co. | Heterocyclic nitrogen compounds--organometallic salt complexes as corrosion inhibitors in lubricating oils |
| US4676917A (en) * | 1986-02-27 | 1987-06-30 | Texaco Inc. | Railway diesel crankcase lubricant |
| US4705642A (en) * | 1986-06-09 | 1987-11-10 | Texaco Inc. | Haze, oxidation, and corrosion resistant diesel engine lubricant |
| EP0315293A3 (en) * | 1987-11-02 | 1989-09-06 | Texaco Development Corporation | Oxidation and corrosion resistant diesel engine lubricant |
| US4938883A (en) * | 1988-08-26 | 1990-07-03 | Amoco Corporation | Overbased alkaline earth alkenyl succinates as a silver-mild source of alkalinity for heavy duty diesel engines |
| US4897086A (en) * | 1988-12-29 | 1990-01-30 | Mobil Oil Corporation | Lubricant and fuel compositions containing reaction products of polyalkenyl succinimides, aldehydes, and triazoles |
| WO1990007563A1 (en) * | 1988-12-29 | 1990-07-12 | Mobil Oil Corporation | Reaction products of polyalkenyl succinimides, aldehydes, and triazoles and lubricant and fuel compositions containing same |
| US4963278A (en) * | 1988-12-29 | 1990-10-16 | Mobil Oil Corporation | Lubricant and fuel compositions containing reaction products of polyalkenyl succinimides, aldehydes, and triazoles |
| US4994197A (en) * | 1989-12-18 | 1991-02-19 | Mobil Oil Corporation | Triazole compositions as fuel and lube additives |
| US5171462A (en) * | 1991-12-23 | 1992-12-15 | Texaco Inc. | Mixtures of polyoxyalkylene ester and aminopolyazoles as oxidation and corrosion resistant lubricant additives |
| US5308521A (en) * | 1992-07-08 | 1994-05-03 | The Lubrizol Corporation | Lubricant with improved anti-corrosion properties |
| US5457083A (en) * | 1992-10-15 | 1995-10-10 | Calgon Corporation | Synergistic antimicrobial combination of polyether phosphonates and non-oxidizing biocides |
| US5397486A (en) * | 1993-07-30 | 1995-03-14 | Chevron Chemical Company | Lubricating oil compositions for railroad diesel engines |
| US6248701B1 (en) * | 1994-05-13 | 2001-06-19 | Henkel Corporation | Aqueous metal coating composition and process with reduced staining and corrosion |
| US5853435A (en) * | 1994-12-30 | 1998-12-29 | Mobil Oil Corporation | Polymeric amine-heterocyclic reaction products as fuel and lubricant antiwear, detergency and cleanliness additives |
| EP0812833A1 (en) * | 1996-06-10 | 1997-12-17 | Armstrong World Industries, Inc. | Water soluble triazole derivatives and their use as blowing inhibitor in chemical embossing processes |
| US5824721A (en) * | 1996-06-10 | 1998-10-20 | Armstrong World Industries, Inc. | Water soluble triazole derivative embossing inhibitor and the use thereof |
| US5888255A (en) * | 1997-10-10 | 1999-03-30 | Exxon Research And Engineering Co. | Distillate fuel composition of reduced nickel corrosivity |
| US20110293469A1 (en) * | 2010-05-28 | 2011-12-01 | John Richardson | Additive formulation for industrial cooling systems |
| US8828273B2 (en) * | 2010-05-28 | 2014-09-09 | Chemtreat, Inc. | Additive formulation for industrial cooling systems |
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